Though his rise to fame since American Idol has seemed meteoric, Simon says he suffered terrible failures before hitting it big. "I made some absolutely horrific mistakes. I believed my own ego, believed my own hype, believed my own abilities, and lots of times it came crashing down," he says. "I thought I was absolutely untouchable. But it was rather like what the world went through two years ago. It was all borrowed. It was all nothing. And sure enough, the whole lot came crashing down. Which meant at the age of 30, I went to live with my mom and dad and had to sell the house, the Porsche—everything went. I had literally nothing other than about a half-million-dollar loan I had to repay."
But this failure served as a wake-up call, Simon says. "Once everything was gone, there was nothing I missed, and all the pressure went away. Then it kind of became reality, which was, I've literally got to start again with nothing." It took three or four years to pay back loans, Simon says, and then he started over. "In a weird way, it was one of the happiest times of my life."
Even when he had the Porsche and the fancy house, Simon says he never could have imagined the level of success he's reached today. "I do sometimes think, which is probably what still drives me—even though the memory of when I lost everything isn't a painful memory now, it's still a reality—many, many times I do actually think, 'Maybe the whole lot will come crashing down,'" he says.